Chemistry:Oxicam
Oxicam is a class of non-steroidal anti-inflammatory drugs (NSAIDs),[2] meaning that they have anti-inflammatory, analgesic, and antipyretic therapeutic effects. Oxicams bind closely to plasma proteins.[1] Most oxicams are unselective inhibitors of the cyclooxygenase (COX) enzymes. The exception is meloxicam with a slight (10:1) preference for COX-2, which, however, is only clinically relevant at low doses.[3]
The most popular drug of the oxicam class is piroxicam.[1] Other examples include: ampiroxicam, droxicam, pivoxicam, tenoxicam, lornoxicam,[1] and meloxicam.
Isoxicam has been suspended as a result of fatal skin reactions.[1]
Chemistry
The physico-chemical characteristics of these molecules vary greatly depending upon the environment.[4]
In contrast to most other NSAIDs, oxicams are not carboxylic acids. They are tautomeric, and can exist as a number of tautomers (keto-enol tautomerism), here exemplified by piroxicam:[2]
Side effects
The oxicams are associated with drug-related erythema multiforme (EM), Stevens–Johnson syndrome, and toxic epidermal necrolysis (TEN). This association is one of the reasons oxicams are not regularly prescribed.
References
- ↑ 1.0 1.1 1.2 1.3 1.4 "Pharmacokinetics of oxicam nonsteroidal anti-inflammatory agents". Clinical Pharmacokinetics 26 (2): 107–20. February 1994. doi:10.2165/00003088-199426020-00004. PMID 8162655.
- ↑ 2.0 2.1 "Tautomeric transformations of piroxicam in solution: a combined experimental and theoretical study". RSC Advances (England, UK: Royal Society of Chemistry) 5 (40): 31852–31860. March 2015. doi:10.1039/c5ra03653d. Bibcode: 2015RSCAd...531852I.
- ↑ Mutschler, Ernst; Gerd Geisslinger; Heyo K. Kroemer; Monika Schäfer-Korting (2001) (in German). Mutschler Arzneimittelwirkungen: Lehrbuch der Pharmakologie und Toxikologie ; mit einführenden Kapiteln in die Anatomie, Physiologie und Pathophysiologie (8 ed.). Stuttgart, Germany: Wissenschaftliche Verlagsgesellschaft. p. 233. ISBN 3-8047-1763-2. OCLC 48723029.
- ↑ "Photophysical studies of oxicam group of NSAIDs: piroxicam, meloxicam and tenoxicam". Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy (Elsevier) 59 (6): 1213–22. April 2003. doi:10.1016/S1386-1425(02)00300-1. PMID 12659890. Bibcode: 2003AcSpA..59.1213B.
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